‘On-water’ organic synthesis: a green, highly efficient, low cost and reusable catalyst system for biaryl synthesis under aerobic conditions at room temperature

Abstract

A simple, greener, efficient, low cost and mild protocol has been developed for sucrose assisted palladium-catalyzed Suzuki reactions in water at room temperature under aerobic condition. The results demonstrate that the sucrose played a 10 crucial role making this protocol a highly efficient. The PdCl 2 /Sucrose/K 2 CO 3 /H 2 O system showed the superb catalytic activity towards the Suzuki reaction of a wide range of aryl/heteroaryl halides with different substituted phenylboronic acids. This method offers an attractive 15 alternative to the existing protocols since the reaction proceeds in aqueous media at room temperature under operational simplicity, shorter reaction time, cost-effective and also provides the products in high yields. The catalytic system is highly recyclable, allowing the reuse of the 20 palladium catalyst in subsequent catalytic runs without significant loss of activity.New advances in cross-coupling techniques have made very significant contribution to organic synthesis as well as pharmaceutical, agricultural and advanced functional materials. 1

Rapid Suzuki-Miyaura Couplings with ppm Level of Palladium Catalyst in a High-Pressure and High-Temperature Water System

“…Increasing concerns about the development of sustainable chemical technologies, mean there have been huge demands for processes which combine high production efficiency with low environmental burden, process safety, and economic viability. From this perspective, utilization of water as a reaction medium would be one of the most attractive solutions for a chemical process [1][2][3][4][5][6][7]. Water is highly abundant, chemically stable, non-toxic, cost-effective and safe compared with most volatile organic solvents used in traditional chemical synthesis.…”

Water Extract of Onion Peel Ash: An Efficient Green Catalytic System for the Synthesis of Isoindoline-1,3-Dione Derivatives

“…To date, numerous organic transformations have been carried out efficiently using these green and recyclable catalytic systems. Examples include the Suzuki-Miyaura reaction [13], synthesis of biaryls [14], Sonogashira reaction [15], Henry reaction [16], Dakin reaction [17] and so on. Based on a survey, the world generates approximately a million tons of bio-wastes monthly [18].…”

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

“…Langer and co-workers [ 36 ] provided a green protocol so that dihydroquinazolinons can be prepared in H 2 O with good yields, whereas quinazolinones can only be obtained by adding oxidant TBHP(tert-butyl hydroperoxide). In the context of green chemistry, water was widely explored as a solvent in various reactions [ 40 , 41 , 42 , 43 ], not only due to its low cost, non-toxicity, easy availability, and eco-benign features, but also because the theoretical and practical advantages of water substantially improved the “on-water” reaction [ 44 , 45 , 46 ]. To date, water has never been used as media to synthesize quinazolinones directly without adding any oxidant.…”